Syntheses and rearrangements of C11H10O ketones derived from homooctavalene - I1 copper-catalyzed decomposition of homooctavalenyldiazomethylketone

✍ Scribed by Tsutomu Miyashi; Tetsuo Nakajo; Heizan Kawamoto; Kimio Akiyama; Toshio Mukai

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 240 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)85909-8

✦ Synopsis

In recent years, much attention has been focused on syntheses and rearrangements of reactive CllHloO ketones'"' which are of interest as potential precursors for (CH)ll+ cations10"13 and (CH),, hydrocarbons.14 In the present and following'4 papers, we wish to report syntheses, ther- mal and BF,-catalyzed rearrangements of several CllHloO ketones derived from the readily accessible endo-8-carboxytricyclo[5.2.0.02'9]nona-3,5-diene (2).15 In this paper, we also report the revised structure of the pyrolysis product of (11) which was previously assigned to (9).16 The carboxylic acid (2) was prepared by photolysis of the diazoketone (1)15 in 45% yield. Chlorination of (2) with SOClz-HMPA was the most successful method to give (3) [UK:", 1800 cm-'] 0 \ 2, R=OH